#------------------------------------------------------------------------------ #$Date: 2021-09-29 03:38:28 +0300 (Wed, 29 Sep 2021) $ #$Revision: 269356 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060972.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7060972 loop_ _publ_author_name 'Zhou, Yuan' 'Liu, Tingting' 'Zheng, Shuang' 'Wang, Xinyuan' 'Zhang, Mei' 'Majeed, Irfan' 'Zhang, Yuanyuan' 'Wang, Hui' 'Zeng, Zhuo' _publ_section_title ; A high selection visually paper detector for hydrazine and MCL luminogens based on fluorinated-pyrrole functionalized triphenylamine ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03642D _journal_year 2021 _chemical_formula_sum 'C32 H22 N4' _chemical_formula_weight 462.53 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2021-06-22 deposited with the CCDC. 2021-09-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.9114(12) _cell_length_b 8.4024(6) _cell_length_c 35.811(3) _cell_measurement_reflns_used 8908 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 49.699 _cell_measurement_theta_min 5.328 _cell_volume 5088.6(7) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1382 _diffrn_reflns_av_unetI/netI 0.0466 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_number 76672 _diffrn_reflns_point_group_measured_fraction_full 0.969 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.574 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.207 _exptl_crystal_description prismatic _exptl_crystal_F_000 1936 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.187 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef 0.0026(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 4465 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0574 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+1.4260P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1348 _refine_ls_wR_factor_ref 0.1627 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2797 _reflns_number_total 4465 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03642d2.cif _cod_data_source_block mo_d8v17613_0m _cod_original_cell_volume 5088.6(6) _cod_database_code 7060972 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.986 _shelx_estimated_absorpt_t_max 0.992 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mo_d8v17613_0m_a.res in Pbca CELL 0.71073 16.9114 8.4024 35.811 90 90 90 ZERR 8 0.0012 0.0006 0.0025 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N UNIT 256 176 32 OMIT 0 6 0 OMIT 0 0 4 OMIT 1 0 2 OMIT -3.00 50.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 wpdb -1 size 0.20 0.17 0.11 mpla c19 > c24 mpla c25 > c30 mpla c13 > c18 mpla c7 > c12 mpla n1 c3 > c6 htab conf EQIV $1 -x+1/2, y-1/2, z HTAB C8 N4_$1 TEMP 23 WGHT 0.063800 1.426000 EXTI 0.002634 FVAR 0.21676 N1 3 0.509483 0.250544 0.521717 11.00000 0.05534 0.05737 = 0.05314 -0.00280 0.00652 -0.00037 N2 3 0.511853 0.301660 0.798565 11.00000 0.07628 0.07436 = 0.05165 -0.00168 -0.00070 -0.00821 N3 3 0.257637 0.350965 0.444000 11.00000 0.08179 0.24504 = 0.08536 -0.03243 -0.00983 -0.03609 N4 3 0.237522 0.651627 0.541991 11.00000 0.09821 0.14655 = 0.09616 0.01351 0.00973 0.05387 C1 1 0.323031 0.465426 0.501979 11.00000 0.05254 0.07907 = 0.05536 0.00880 0.00119 -0.00330 C2 1 0.393919 0.420073 0.515188 11.00000 0.05921 0.06048 = 0.05069 0.00185 0.00063 -0.00419 AFIX 43 H2 2 0.408307 0.464553 0.537977 11.00000 -1.20000 AFIX 0 C3 1 0.449776 0.314410 0.499403 11.00000 0.05519 0.05686 = 0.04818 0.00017 0.00045 -0.00653 C4 1 0.465387 0.267576 0.463165 11.00000 0.07699 0.06766 = 0.05070 -0.00438 0.00412 -0.01234 AFIX 43 H4 2 0.435155 0.292429 0.442270 11.00000 -1.20000 AFIX 0 C5 1 0.533912 0.177141 0.463352 11.00000 0.09101 0.07030 = 0.05792 -0.01220 0.02002 -0.00393 AFIX 43 H5 2 0.558053 0.131461 0.442626 11.00000 -1.20000 AFIX 0 C6 1 0.559669 0.167100 0.499456 11.00000 0.06635 0.06074 = 0.07399 -0.00361 0.01907 0.00532 AFIX 43 H6 2 0.604270 0.112125 0.507482 11.00000 -1.20000 AFIX 0 C7 1 0.511751 0.258678 0.561496 11.00000 0.04915 0.05114 = 0.05377 0.00259 0.00090 0.00225 C8 1 0.444667 0.221030 0.582014 11.00000 0.04995 0.06170 = 0.05863 0.00185 -0.00214 -0.00447 AFIX 43 H8 2 0.398899 0.188127 0.569861 11.00000 -1.20000 AFIX 0 C9 1 0.445913 0.232399 0.620286 11.00000 0.05163 0.06278 = 0.05621 0.00392 0.00488 -0.00398 AFIX 43 H9 2 0.400468 0.207768 0.633719 11.00000 -1.20000 AFIX 0 C10 1 0.513710 0.280005 0.639491 11.00000 0.05455 0.04972 = 0.05544 0.00455 0.00009 0.00094 C11 1 0.579983 0.315512 0.618090 11.00000 0.04797 0.07316 = 0.06114 0.00337 -0.00504 -0.00550 AFIX 43 H11 2 0.626159 0.347180 0.630078 11.00000 -1.20000 AFIX 0 C12 1 0.579464 0.305323 0.579779 11.00000 0.04757 0.06936 = 0.06207 0.00219 0.00648 -0.00261 AFIX 43 H12 2 0.624781 0.329903 0.566245 11.00000 -1.20000 AFIX 0 C13 1 0.513892 0.288863 0.680482 11.00000 0.05949 0.04907 = 0.05635 0.00323 -0.00235 -0.00228 C14 1 0.448870 0.343349 0.700432 11.00000 0.06093 0.05792 = 0.05918 0.00454 -0.00242 0.00371 AFIX 43 H14 2 0.404166 0.376262 0.687428 11.00000 -1.20000 AFIX 0 C15 1 0.448481 0.350154 0.738636 11.00000 0.07011 0.05870 = 0.05802 -0.00083 0.00391 0.00341 AFIX 43 H15 2 0.404144 0.388991 0.751005 11.00000 -1.20000 AFIX 0 C16 1 0.513595 0.299679 0.759129 11.00000 0.07161 0.05050 = 0.05270 0.00051 0.00042 -0.00256 C17 1 0.579292 0.245663 0.739658 11.00000 0.06719 0.05877 = 0.05778 -0.00052 -0.00692 0.00418 AFIX 43 H17 2 0.623814 0.212213 0.752726 11.00000 -1.20000 AFIX 0 C18 1 0.579324 0.241031 0.701324 11.00000 0.06414 0.05663 = 0.05882 -0.00069 0.00120 0.00259 AFIX 43 H18 2 0.624217 0.205004 0.688935 11.00000 -1.20000 AFIX 0 C19 1 0.439429 0.270700 0.817414 11.00000 0.07712 0.05935 = 0.05167 0.00390 0.00258 0.00494 C20 1 0.389538 0.151556 0.805189 11.00000 0.08154 0.06467 = 0.06759 0.00444 0.00253 0.00198 AFIX 43 H20 2 0.403498 0.090696 0.784524 11.00000 -1.20000 AFIX 0 C21 1 0.318900 0.121937 0.823442 11.00000 0.08135 0.08982 = 0.08673 0.01834 0.00096 -0.00364 AFIX 43 H21 2 0.285196 0.042838 0.814687 11.00000 -1.20000 AFIX 0 C22 1 0.298618 0.208071 0.854122 11.00000 0.08061 0.11307 = 0.08419 0.02364 0.01036 0.02165 AFIX 43 H22 2 0.251560 0.186601 0.866580 11.00000 -1.20000 AFIX 0 C23 1 0.347390 0.326144 0.866635 11.00000 0.10828 0.09343 = 0.06734 0.00449 0.01549 0.03499 AFIX 43 H23 2 0.333136 0.385025 0.887569 11.00000 -1.20000 AFIX 0 C24 1 0.417988 0.359249 0.848460 11.00000 0.10176 0.06895 = 0.06131 0.00008 0.00616 0.01104 AFIX 43 H24 2 0.450697 0.440328 0.857058 11.00000 -1.20000 AFIX 0 C25 1 0.581458 0.328708 0.819497 11.00000 0.08040 0.06748 = 0.05766 -0.01080 -0.00398 0.00864 C26 1 0.595560 0.243472 0.851703 11.00000 0.10600 0.09876 = 0.06162 -0.00287 -0.00549 0.02176 AFIX 43 H26 2 0.560139 0.165388 0.859382 11.00000 -1.20000 AFIX 0 C27 1 0.662702 0.274675 0.872557 11.00000 0.12374 0.15117 = 0.06698 -0.01307 -0.01638 0.05531 AFIX 43 H27 2 0.671447 0.219081 0.894630 11.00000 -1.20000 AFIX 0 C28 1 0.716416 0.386424 0.861081 11.00000 0.09317 0.17649 = 0.10015 -0.05484 -0.02980 0.04341 AFIX 43 H28 2 0.761609 0.405650 0.875174 11.00000 -1.20000 AFIX 0 C29 1 0.703416 0.469673 0.828840 11.00000 0.08355 0.11785 = 0.10641 -0.04402 -0.01000 0.00144 AFIX 43 H29 2 0.740177 0.544538 0.820809 11.00000 -1.20000 AFIX 0 C30 1 0.635924 0.442729 0.808254 11.00000 0.08520 0.08013 = 0.07597 -0.01838 -0.00490 -0.00155 AFIX 43 H30 2 0.626762 0.501361 0.786657 11.00000 -1.20000 AFIX 0 C31 1 0.288129 0.402769 0.469109 11.00000 0.05531 0.13883 = 0.06660 -0.00067 -0.00146 -0.01450 C32 1 0.275184 0.570009 0.523770 11.00000 0.06260 0.09920 = 0.06989 0.01577 0.00095 0.01442 HKLF 4 REM mo_d8v17613_0m_a.res in Pbca REM R1 = 0.0574 for 2797 Fo > 4sig(Fo) and 0.0995 for all 4465 data REM 326 parameters refined using 0 restraints END WGHT 0.0610 1.4921 REM Instructions for potential hydrogen bonds HTAB C8 N4_$1 REM Highest difference peak 0.187, deepest hole -0.176, 1-sigma level 0.046 Q1 1 0.5411 0.2453 0.6312 11.00000 0.05 0.19 Q2 1 0.5403 0.2207 0.5700 11.00000 0.05 0.17 Q3 1 0.4932 0.2689 0.6319 11.00000 0.05 0.17 Q4 1 0.5122 0.2544 0.5424 11.00000 0.05 0.16 Q5 1 0.2383 0.0024 0.7498 11.00000 0.05 0.16 Q6 1 0.4832 0.2771 0.5125 11.00000 0.05 0.15 Q7 1 0.4770 0.2633 0.6911 11.00000 0.05 0.15 Q8 1 0.2279 0.4919 0.5448 11.00000 0.05 0.15 Q9 1 0.4942 0.2475 0.8616 11.00000 0.05 0.15 Q10 1 0.7842 0.4816 0.8656 11.00000 0.05 0.14 Q11 1 0.5368 0.2467 0.6891 11.00000 0.05 0.14 Q12 1 0.4875 0.2226 0.5702 11.00000 0.05 0.14 Q13 1 0.3111 0.4375 0.4391 11.00000 0.05 0.13 Q14 1 0.2210 0.0253 0.8578 11.00000 0.05 0.13 Q15 1 0.2559 -0.0121 0.8699 11.00000 0.05 0.13 Q16 1 0.6984 0.4577 0.7464 11.00000 0.05 0.13 Q17 1 0.4795 0.2452 0.7491 11.00000 0.05 0.13 Q18 1 0.2611 -0.0279 0.8186 11.00000 0.05 0.12 Q19 1 0.2523 0.5163 0.4998 11.00000 0.05 0.12 Q20 1 0.5430 0.2527 0.8007 11.00000 0.05 0.12 ; _shelx_res_checksum 63987 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.50948(10) 0.2505(2) 0.52172(5) 0.0553(5) Uani 1 1 d . . . . . N2 N 0.51185(12) 0.3017(3) 0.79857(5) 0.0674(6) Uani 1 1 d . . . . . N3 N 0.25764(16) 0.3510(5) 0.44400(8) 0.1374(14) Uani 1 1 d . . . . . N4 N 0.23752(17) 0.6516(4) 0.54199(8) 0.1136(11) Uani 1 1 d . . . . . C1 C 0.32303(14) 0.4654(3) 0.50198(7) 0.0623(7) Uani 1 1 d . . . . . C2 C 0.39392(14) 0.4201(3) 0.51519(6) 0.0568(6) Uani 1 1 d . . . . . H2 H 0.4083 0.4646 0.5380 0.068 Uiso 1 1 calc R U . . . C3 C 0.44978(13) 0.3144(3) 0.49940(6) 0.0534(6) Uani 1 1 d . . . . . C4 C 0.46539(16) 0.2676(3) 0.46316(7) 0.0651(7) Uani 1 1 d . . . . . H4 H 0.4352 0.2924 0.4423 0.078 Uiso 1 1 calc R U . . . C5 C 0.53391(17) 0.1771(3) 0.46335(7) 0.0731(8) Uani 1 1 d . . . . . H5 H 0.5581 0.1315 0.4426 0.088 Uiso 1 1 calc R U . . . C6 C 0.55967(15) 0.1671(3) 0.49946(7) 0.0670(7) Uani 1 1 d . . . . . H6 H 0.6043 0.1121 0.5075 0.080 Uiso 1 1 calc R U . . . C7 C 0.51175(12) 0.2587(3) 0.56150(6) 0.0514(6) Uani 1 1 d . . . . . C8 C 0.44467(13) 0.2210(3) 0.58201(6) 0.0568(6) Uani 1 1 d . . . . . H8 H 0.3989 0.1881 0.5699 0.068 Uiso 1 1 calc R U . . . C9 C 0.44591(13) 0.2324(3) 0.62029(6) 0.0569(6) Uani 1 1 d . . . . . H9 H 0.4005 0.2078 0.6337 0.068 Uiso 1 1 calc R U . . . C10 C 0.51371(13) 0.2800(3) 0.63949(6) 0.0532(6) Uani 1 1 d . . . . . C11 C 0.57998(13) 0.3155(3) 0.61809(7) 0.0608(6) Uani 1 1 d . . . . . H11 H 0.6262 0.3472 0.6301 0.073 Uiso 1 1 calc R U . . . C12 C 0.57946(13) 0.3053(3) 0.57978(6) 0.0597(6) Uani 1 1 d . . . . . H12 H 0.6248 0.3299 0.5662 0.072 Uiso 1 1 calc R U . . . C13 C 0.51389(13) 0.2889(3) 0.68048(7) 0.0550(6) Uani 1 1 d . . . . . C14 C 0.44887(14) 0.3433(3) 0.70043(6) 0.0593(6) Uani 1 1 d . . . . . H14 H 0.4042 0.3763 0.6874 0.071 Uiso 1 1 calc R U . . . C15 C 0.44848(15) 0.3502(3) 0.73864(6) 0.0623(7) Uani 1 1 d . . . . . H15 H 0.4041 0.3890 0.7510 0.075 Uiso 1 1 calc R U . . . C16 C 0.51359(14) 0.2997(3) 0.75913(6) 0.0583(6) Uani 1 1 d . . . . . C17 C 0.57929(15) 0.2457(3) 0.73966(6) 0.0612(6) Uani 1 1 d . . . . . H17 H 0.6238 0.2122 0.7527 0.073 Uiso 1 1 calc R U . . . C18 C 0.57932(15) 0.2410(3) 0.70132(6) 0.0599(6) Uani 1 1 d . . . . . H18 H 0.6242 0.2050 0.6889 0.072 Uiso 1 1 calc R U . . . C19 C 0.43943(15) 0.2707(3) 0.81741(7) 0.0627(7) Uani 1 1 d . . . . . C20 C 0.38954(16) 0.1516(3) 0.80519(7) 0.0713(7) Uani 1 1 d . . . . . H20 H 0.4035 0.0907 0.7845 0.086 Uiso 1 1 calc R U . . . C21 C 0.31890(18) 0.1219(4) 0.82344(9) 0.0860(9) Uani 1 1 d . . . . . H21 H 0.2852 0.0428 0.8147 0.103 Uiso 1 1 calc R U . . . C22 C 0.29862(19) 0.2081(5) 0.85412(10) 0.0926(10) Uani 1 1 d . . . . . H22 H 0.2516 0.1866 0.8666 0.111 Uiso 1 1 calc R U . . . C23 C 0.3474(2) 0.3261(4) 0.86663(8) 0.0897(9) Uani 1 1 d . . . . . H23 H 0.3331 0.3850 0.8876 0.108 Uiso 1 1 calc R U . . . C24 C 0.41799(18) 0.3592(3) 0.84846(7) 0.0773(8) Uani 1 1 d . . . . . H24 H 0.4507 0.4403 0.8571 0.093 Uiso 1 1 calc R U . . . C25 C 0.58146(17) 0.3287(3) 0.81950(7) 0.0685(7) Uani 1 1 d . . . . . C26 C 0.5956(2) 0.2435(4) 0.85170(8) 0.0888(9) Uani 1 1 d . . . . . H26 H 0.5601 0.1654 0.8594 0.107 Uiso 1 1 calc R U . . . C27 C 0.6627(3) 0.2747(6) 0.87256(10) 0.1140(13) Uani 1 1 d . . . . . H27 H 0.6714 0.2191 0.8946 0.137 Uiso 1 1 calc R U . . . C28 C 0.7164(2) 0.3864(6) 0.86108(13) 0.1233(16) Uani 1 1 d . . . . . H28 H 0.7616 0.4057 0.8752 0.148 Uiso 1 1 calc R U . . . C29 C 0.70342(19) 0.4697(5) 0.82884(11) 0.1026(11) Uani 1 1 d . . . . . H29 H 0.7402 0.5445 0.8208 0.123 Uiso 1 1 calc R U . . . C30 C 0.63592(17) 0.4427(4) 0.80825(8) 0.0804(8) Uani 1 1 d . . . . . H30 H 0.6268 0.5014 0.7867 0.097 Uiso 1 1 calc R U . . . C31 C 0.28813(16) 0.4028(4) 0.46911(8) 0.0869(9) Uani 1 1 d . . . . . C32 C 0.27518(17) 0.5700(4) 0.52377(8) 0.0772(8) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0553(12) 0.0574(12) 0.0531(12) -0.0028(9) 0.0065(9) -0.0004(10) N2 0.0763(15) 0.0744(15) 0.0516(12) -0.0017(10) -0.0007(11) -0.0082(12) N3 0.0818(19) 0.245(4) 0.0854(19) -0.032(2) -0.0098(17) -0.036(2) N4 0.098(2) 0.147(3) 0.0962(19) 0.0135(19) 0.0097(16) 0.054(2) C1 0.0525(15) 0.0791(18) 0.0554(14) 0.0088(13) 0.0012(12) -0.0033(13) C2 0.0592(15) 0.0605(15) 0.0507(13) 0.0018(11) 0.0006(11) -0.0042(12) C3 0.0552(14) 0.0569(14) 0.0482(13) 0.0002(11) 0.0004(11) -0.0065(12) C4 0.0770(17) 0.0677(17) 0.0507(15) -0.0044(12) 0.0041(13) -0.0123(14) C5 0.091(2) 0.0703(18) 0.0579(17) -0.0122(13) 0.0200(15) -0.0039(16) C6 0.0663(16) 0.0607(16) 0.0740(18) -0.0036(13) 0.0191(14) 0.0053(13) C7 0.0492(13) 0.0511(14) 0.0538(14) 0.0026(11) 0.0009(11) 0.0022(11) C8 0.0500(14) 0.0617(15) 0.0586(15) 0.0019(12) -0.0021(11) -0.0045(11) C9 0.0516(14) 0.0628(15) 0.0562(15) 0.0039(11) 0.0049(11) -0.0040(12) C10 0.0545(14) 0.0497(14) 0.0554(14) 0.0045(11) 0.0001(11) 0.0009(11) C11 0.0480(13) 0.0732(17) 0.0611(15) 0.0034(13) -0.0050(12) -0.0055(12) C12 0.0476(13) 0.0694(16) 0.0621(16) 0.0022(13) 0.0065(12) -0.0026(12) C13 0.0595(15) 0.0491(14) 0.0563(14) 0.0032(11) -0.0024(12) -0.0023(11) C14 0.0609(15) 0.0579(15) 0.0592(15) 0.0045(12) -0.0024(12) 0.0037(12) C15 0.0701(16) 0.0587(15) 0.0580(15) -0.0008(12) 0.0039(13) 0.0034(13) C16 0.0716(16) 0.0505(14) 0.0527(15) 0.0005(11) 0.0004(12) -0.0026(12) C17 0.0672(16) 0.0588(16) 0.0578(16) -0.0005(12) -0.0069(12) 0.0042(13) C18 0.0641(15) 0.0566(15) 0.0588(16) -0.0007(12) 0.0012(12) 0.0026(12) C19 0.0771(17) 0.0594(16) 0.0517(15) 0.0039(12) 0.0026(13) 0.0049(14) C20 0.0815(19) 0.0647(17) 0.0676(16) 0.0044(13) 0.0025(14) 0.0020(15) C21 0.081(2) 0.090(2) 0.087(2) 0.0183(18) 0.0010(17) -0.0036(17) C22 0.081(2) 0.113(3) 0.084(2) 0.024(2) 0.0104(18) 0.022(2) C23 0.108(2) 0.093(2) 0.0673(19) 0.0045(17) 0.0155(19) 0.035(2) C24 0.102(2) 0.0689(18) 0.0613(16) 0.0001(14) 0.0062(16) 0.0110(16) C25 0.0804(18) 0.0675(17) 0.0577(16) -0.0108(13) -0.0040(14) 0.0086(15) C26 0.106(2) 0.099(2) 0.0616(18) -0.0029(16) -0.0055(17) 0.0218(19) C27 0.124(3) 0.151(4) 0.067(2) -0.013(2) -0.016(2) 0.055(3) C28 0.093(3) 0.176(5) 0.100(3) -0.055(3) -0.030(2) 0.043(3) C29 0.084(2) 0.118(3) 0.106(3) -0.044(2) -0.010(2) 0.001(2) C30 0.085(2) 0.080(2) 0.0760(19) -0.0184(15) -0.0049(16) -0.0015(17) C31 0.0553(16) 0.139(3) 0.0666(18) -0.0007(18) -0.0015(15) -0.0145(18) C32 0.0626(17) 0.099(2) 0.0699(18) 0.0158(17) 0.0010(14) 0.0144(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C3 108.3(2) . . ? C6 N1 C7 126.4(2) . . ? C3 N1 C7 124.96(18) . . ? C16 N2 C25 121.0(2) . . ? C16 N2 C19 119.4(2) . . ? C25 N2 C19 119.6(2) . . ? C2 C1 C31 123.9(3) . . ? C2 C1 C32 119.2(2) . . ? C31 C1 C32 116.5(2) . . ? C1 C2 C3 129.3(2) . . ? C1 C2 H2 115.4 . . ? C3 C2 H2 115.4 . . ? C4 C3 N1 106.9(2) . . ? C4 C3 C2 133.0(2) . . ? N1 C3 C2 119.7(2) . . ? C3 C4 C5 108.1(2) . . ? C3 C4 H4 125.9 . . ? C5 C4 H4 125.9 . . ? C6 C5 C4 107.8(2) . . ? C6 C5 H5 126.1 . . ? C4 C5 H5 126.1 . . ? N1 C6 C5 108.9(2) . . ? N1 C6 H6 125.5 . . ? C5 C6 H6 125.5 . . ? C12 C7 C8 119.5(2) . . ? C12 C7 N1 120.74(19) . . ? C8 C7 N1 119.71(19) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.6(2) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 116.9(2) . . ? C11 C10 C13 122.6(2) . . ? C9 C10 C13 120.6(2) . . ? C12 C11 C10 122.1(2) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C7 119.9(2) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 116.6(2) . . ? C14 C13 C10 121.9(2) . . ? C18 C13 C10 121.5(2) . . ? C15 C14 C13 122.1(2) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 120.7(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 118.0(2) . . ? C17 C16 N2 121.5(2) . . ? C15 C16 N2 120.5(2) . . ? C18 C17 C16 120.8(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C13 121.8(2) . . ? C17 C18 H18 119.1 . . ? C13 C18 H18 119.1 . . ? C20 C19 C24 118.9(3) . . ? C20 C19 N2 120.6(2) . . ? C24 C19 N2 120.5(3) . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C19 C24 C23 119.6(3) . . ? C19 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C26 C25 C30 119.1(3) . . ? C26 C25 N2 120.3(3) . . ? C30 C25 N2 120.6(2) . . ? C25 C26 C27 119.7(4) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 120.8(4) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C29 C28 C27 119.8(4) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.1(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C25 120.5(3) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? N3 C31 C1 176.9(3) . . ? N4 C32 C1 178.3(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.359(3) . ? N1 C3 1.395(3) . ? N1 C7 1.427(3) . ? N2 C16 1.413(3) . ? N2 C25 1.414(3) . ? N2 C19 1.422(3) . ? N3 C31 1.124(3) . ? N4 C32 1.141(4) . ? C1 C2 1.344(3) . ? C1 C31 1.418(4) . ? C1 C32 1.427(4) . ? C2 C3 1.414(3) . ? C2 H2 0.9300 . ? C3 C4 1.382(3) . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? C5 C6 1.367(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.376(3) . ? C7 C8 1.388(3) . ? C8 C9 1.374(3) . ? C8 H8 0.9300 . ? C9 C10 1.396(3) . ? C9 H9 0.9300 . ? C10 C11 1.390(3) . ? C10 C13 1.470(3) . ? C11 C12 1.375(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.389(3) . ? C13 C18 1.394(3) . ? C14 C15 1.369(3) . ? C14 H14 0.9300 . ? C15 C16 1.390(3) . ? C15 H15 0.9300 . ? C16 C17 1.388(3) . ? C17 C18 1.373(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.380(3) . ? C19 C24 1.386(3) . ? C20 C21 1.384(4) . ? C20 H20 0.9300 . ? C21 C22 1.360(4) . ? C21 H21 0.9300 . ? C22 C23 1.366(4) . ? C22 H22 0.9300 . ? C23 C24 1.388(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.378(4) . ? C25 C30 1.389(4) . ? C26 C27 1.384(5) . ? C26 H26 0.9300 . ? C27 C28 1.370(5) . ? C27 H27 0.9300 . ? C28 C29 1.368(5) . ? C28 H28 0.9300 . ? C29 C30 1.377(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8 N4 0.93 2.53 3.448(4) 168.1 8_655 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31 C1 C2 C3 4.6(4) . . . . ? C32 C1 C2 C3 177.6(2) . . . . ? C6 N1 C3 C4 -0.1(3) . . . . ? C7 N1 C3 C4 -174.1(2) . . . . ? C6 N1 C3 C2 -173.7(2) . . . . ? C7 N1 C3 C2 12.3(3) . . . . ? C1 C2 C3 C4 25.5(4) . . . . ? C1 C2 C3 N1 -162.9(2) . . . . ? N1 C3 C4 C5 -0.3(3) . . . . ? C2 C3 C4 C5 172.1(2) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C3 N1 C6 C5 0.5(3) . . . . ? C7 N1 C6 C5 174.4(2) . . . . ? C4 C5 C6 N1 -0.7(3) . . . . ? C6 N1 C7 C12 55.0(3) . . . . ? C3 N1 C7 C12 -132.1(2) . . . . ? C6 N1 C7 C8 -125.8(2) . . . . ? C3 N1 C7 C8 47.1(3) . . . . ? C12 C7 C8 C9 0.8(3) . . . . ? N1 C7 C8 C9 -178.4(2) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C13 -179.1(2) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C13 C10 C11 C12 179.3(2) . . . . ? C10 C11 C12 C7 0.0(4) . . . . ? C8 C7 C12 C11 -0.5(3) . . . . ? N1 C7 C12 C11 178.7(2) . . . . ? C11 C10 C13 C14 142.4(2) . . . . ? C9 C10 C13 C14 -38.6(3) . . . . ? C11 C10 C13 C18 -38.4(3) . . . . ? C9 C10 C13 C18 140.7(2) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? C10 C13 C14 C15 179.3(2) . . . . ? C13 C14 C15 C16 -1.1(4) . . . . ? C14 C15 C16 C17 1.4(4) . . . . ? C14 C15 C16 N2 -177.7(2) . . . . ? C25 N2 C16 C17 32.5(3) . . . . ? C19 N2 C16 C17 -145.4(2) . . . . ? C25 N2 C16 C15 -148.4(2) . . . . ? C19 N2 C16 C15 33.7(3) . . . . ? C15 C16 C17 C18 -0.6(4) . . . . ? N2 C16 C17 C18 178.5(2) . . . . ? C16 C17 C18 C13 -0.4(4) . . . . ? C14 C13 C18 C17 0.7(3) . . . . ? C10 C13 C18 C17 -178.5(2) . . . . ? C16 N2 C19 C20 41.5(3) . . . . ? C25 N2 C19 C20 -136.4(2) . . . . ? C16 N2 C19 C24 -138.8(2) . . . . ? C25 N2 C19 C24 43.3(3) . . . . ? C24 C19 C20 C21 0.6(4) . . . . ? N2 C19 C20 C21 -179.7(2) . . . . ? C19 C20 C21 C22 -1.3(4) . . . . ? C20 C21 C22 C23 1.1(5) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C20 C19 C24 C23 0.3(4) . . . . ? N2 C19 C24 C23 -179.4(2) . . . . ? C22 C23 C24 C19 -0.4(4) . . . . ? C16 N2 C25 C26 -140.0(3) . . . . ? C19 N2 C25 C26 37.9(3) . . . . ? C16 N2 C25 C30 40.9(3) . . . . ? C19 N2 C25 C30 -141.2(2) . . . . ? C30 C25 C26 C27 1.1(4) . . . . ? N2 C25 C26 C27 -178.0(3) . . . . ? C25 C26 C27 C28 -1.7(5) . . . . ? C26 C27 C28 C29 0.7(6) . . . . ? C27 C28 C29 C30 0.9(5) . . . . ? C28 C29 C30 C25 -1.5(5) . . . . ? C26 C25 C30 C29 0.4(4) . . . . ? N2 C25 C30 C29 179.5(2) . . . . ?